Condo
☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere
Photo gallery for ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere





Reviews
9.4 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 7110.4 sq m
Popular amenities
Explore the area

Winter Park, CO
- Place, Hideaway Park1 min walk
- Place, Winter Park Visitor Center3 min walk
- Place, Bella Vita5 min walk
Rooms & beds
2 bedrooms (sleeps 7)
Bunk Room
1 Single Bunk Bed and 1 Single Bed
Primary King Suite
1 King Bed
2 bathrooms
Primary Ensuite Bathroom
Bathtub · Toilet · Shower only
Shared Bathroom
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Dining area
About this property
☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere
Trailhead Lodges 424 is a gorgeous condo with a plethora of amenities including a clubhouse with a gym, heated pool, hot tub, and a communal area with gas grill & fire pits. This home also has a private washer and dryer, and a full spacious kitchen with high-end finishes. The comfortable living room with modern leather furniture boasts a fireplace and a flat screen, plus forest views and a private balcony. This two-bedroom condo is located in an enviable location in one of downtown Winter Park's most popular complexes. This is a prime location downtown, close to Hideaway Park and just a few minute walk to your choice of shops and restaurants. You'll love your stay at Trailhead Lodges 424, which has everything you need for your mountain adventures.
Sleeping Arrangements: Primary King Suite, Full/Full bunk and Twin single in the bunk room, and a Queen pullout couch in the living room. Sleeps up to seven guests.
Local Deals: Save on local adventurous activities, gear rentals, transportation, and more when booking with us.
Please Note:
- Quiet hours begin daily at 10pm. Please respect your neighbors, many of which live nearby year-round.
- This condo is in building 4 on level 2.
- This home does not have air conditioning, but there is a ceiling fan or portable fan in each room.
Luxury Linen Package Included: This home has crisp, white duvet covers that are washed after every stay. Enjoy hotel-style bedding in the comfort of a home.
Parking: There is room for two cars in any open areas around the building.
Location: Trailhead Lodges is located in the center of downtown Winter Park. Just 2 miles to Winter Park Resort and a short, easy walk to shops, restaurants and the free shuttle service in downtown Winter Park.
RENTAL LICENSE NO: 017114
The Winter Park Lodging Company Difference
24/7 Local Help: Book with confidence knowing that the rates, images and details published on this property are 100% accurate. We are conveniently headquartered in Winter Park, this provides us with a local advantage to take care of any issue or need that may arise during your stay, 24/7. If any questions, needs or concerns arise just call us and we will be there at your door to make it right.
Keyless Lock: This home is equipped with a Smart Lock, allowing easy, secure access to your property at check-in and throughout your stay. There's no need to check in at a separate location!
What's Included: Every home is stocked with all your household essentials, high quality sheets and towels, and a starter kit of high-end bathroom products, and an ample supply of laundry detergent, trash bags, dish soap, tissues, etc.
We're Following the Rules: This vacation rental is professionally managed and follows all local & state tax rules. Your reservation total includes all applicable taxes, cleaning fee, and Accidental Property Damage Protection.
Clean & Safe: Keeping our vacation homes sparkling clean is a top priority at Winter Park Lodging Company. All properties are cleaned, sanitized & disinfected before guests check-in with products proven to eliminate viruses & bacteria. All linens are laundered at an offsite facility that meets commercial standards. Additionally, the entirety of our housekeeping processes meet and exceed CDC cleaning guidelines. If you have any questions/concerns, please reach out to our Vacation Planners for more details.
Check-In: This property offers remote check-in upon arrival. Check-in instructions will be sent via email within 48 hours of check-in date once the Rental Agreement is signed.
Sleeping Arrangements: Primary King Suite, Full/Full bunk and Twin single in the bunk room, and a Queen pullout couch in the living room. Sleeps up to seven guests.
Local Deals: Save on local adventurous activities, gear rentals, transportation, and more when booking with us.
Please Note:
- Quiet hours begin daily at 10pm. Please respect your neighbors, many of which live nearby year-round.
- This condo is in building 4 on level 2.
- This home does not have air conditioning, but there is a ceiling fan or portable fan in each room.
Luxury Linen Package Included: This home has crisp, white duvet covers that are washed after every stay. Enjoy hotel-style bedding in the comfort of a home.
Parking: There is room for two cars in any open areas around the building.
Location: Trailhead Lodges is located in the center of downtown Winter Park. Just 2 miles to Winter Park Resort and a short, easy walk to shops, restaurants and the free shuttle service in downtown Winter Park.
RENTAL LICENSE NO: 017114
The Winter Park Lodging Company Difference
24/7 Local Help: Book with confidence knowing that the rates, images and details published on this property are 100% accurate. We are conveniently headquartered in Winter Park, this provides us with a local advantage to take care of any issue or need that may arise during your stay, 24/7. If any questions, needs or concerns arise just call us and we will be there at your door to make it right.
Keyless Lock: This home is equipped with a Smart Lock, allowing easy, secure access to your property at check-in and throughout your stay. There's no need to check in at a separate location!
What's Included: Every home is stocked with all your household essentials, high quality sheets and towels, and a starter kit of high-end bathroom products, and an ample supply of laundry detergent, trash bags, dish soap, tissues, etc.
We're Following the Rules: This vacation rental is professionally managed and follows all local & state tax rules. Your reservation total includes all applicable taxes, cleaning fee, and Accidental Property Damage Protection.
Clean & Safe: Keeping our vacation homes sparkling clean is a top priority at Winter Park Lodging Company. All properties are cleaned, sanitized & disinfected before guests check-in with products proven to eliminate viruses & bacteria. All linens are laundered at an offsite facility that meets commercial standards. Additionally, the entirety of our housekeeping processes meet and exceed CDC cleaning guidelines. If you have any questions/concerns, please reach out to our Vacation Planners for more details.
Check-In: This property offers remote check-in upon arrival. Check-in instructions will be sent via email within 48 hours of check-in date once the Rental Agreement is signed.
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10.0 out of 10, Exceptional, (229 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Winter Park
Located in Winter Park, this condo is in the city centre and in the mountains. Byers Peak Wilderness and Hideaway Park reflect the area's natural beauty and area attractions include Amaze'n Maze Winter Park and Alpine Slide. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Winter Park, CO
What's nearby
- Hideaway Park - 1 min walk - 0.1 km
- Winter Park Visitor Center - 3 min walk - 0.3 km
- Bella Vita - 5 min walk - 0.5 km
- Blue Sky Massage - 7 min walk - 0.6 km
- Grand Park Community Recreation Center - 16 min walk - 1.4 km
Getting around
Restaurants
- Wake N’ Bacon - 12 min walk
- The Noble Buck - 10 min walk
- McDonald's - 5 min walk
- Wendy's - 5 min drive
- Snoasis - 11 min drive
Frequently asked questions
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
7 March 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Mar 2026
Verified
10/10 Excellent
Bradley C.
21 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Bradley C.
Stayed 3 nights in Jan 2026
From a partner site
10/10 Excellent
Anna S.
29 July 2025
Wonderful stay Great location
Anna S.
From a partner site
10/10 Excellent
Norman S.
18 April 2025
Great place
Norman S.
Verified
10/10 Excellent
Natalie G.
13 July 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay
Natalie G.
Stayed 2 nights in Jun 2019
From a partner site
10/10 Excellent
Douglas G.
13 March 2025
Excellent
Douglas G.
Verified
10/10 Excellent
Matthew R.
27 February 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location
Matthew R.
Stayed 4 nights in Feb 2023
Verified
10/10 Excellent
Verified traveller
2 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious and Serene

Verified traveller
Stayed 4 nights in Jul 2025
From a partner site
10/10 Excellent
marc l.
28 December 2023
Holiday season stay
marc l.
Verified
10/10 Excellent
Keaton N.
9 March 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Keaton N.
Stayed 4 nights in Mar 2023
Verified
10/10 Excellent
Shanna T.
15 March 2019
Favorite VRBO ever
Shanna T.
Stayed 4 nights in Mar 2019
Verified
10/10 Excellent
Melissa P.
29 March 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Location & Clean Property
Melissa P.
Stayed 3 nights in Mar 2022
Archival
10/10 Excellent
David R.
1 May 2016
Fantastic location + new building + great staff = great stay!
David R.
Stayed 3 nights in Apr 2016
From a partner site
10/10 Excellent
Linda M.
3 October 2024
Excellent
Linda M.
From a partner site
8/10 Good
Mike B.
27 March 2024
Above Average
Mike B.
Verified
10/10 Excellent
Bryan B.
27 February 2019
Spacious Condo
Bryan B.
Stayed 4 nights in Feb 2019
From a partner site
10/10 Excellent
Joseph S.
4 February 2024
Winter Park Stay - January 2024
Joseph S.
From a partner site
10/10 Excellent
26 July 2022
Excellent
Stayed 4 nights in Jul 2022
Verified
8/10 Good
sharon l.
16 March 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location close to wineries, breweries, and Lift Line stop to slopes
sharon l.
Stayed 5 nights in Mar 2023
From a partner site
10/10 Excellent
stacy c.
28 January 2023
Outstanding!
stacy c.
Verified
8/10 Good
gini K.
31 August 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
spacious but not classy
gini K.
Stayed 3 nights in Aug 2020
From a partner site
2/10 Terrible
SUZIE T.
13 July 2022
Definitely skip WP Seo Monday through Friday if you value peace and quiet
SUZIE T.
Verified
10/10 Excellent
Nicholas J.
19 March 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nicholas J.
Stayed 4 nights in Mar 2026
Verified
10/10 Excellent
Jason S.
18 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jason S.
Stayed 4 nights in Feb 2026
From a partner site
10/10 Excellent
Janessa H.
26 November 2022
Amazing condo
Janessa H.
About the host
Hosted by Winter Park Lodging Company
Winter Park Lodging Company provides custom, stress-free experiences for every type of traveler, offering high-end vacation homes, exceptional customer service, and sharing our passion for mountain living.
The Winter Park Lodging Company Difference
24/7 Local Help: Book with confidence knowing that the rates, images and details published on this property are 100% accurate. We are conveniently headquartered in Winter Park, this provides us with a local advantage to take care of any issue or need that may arise during your stay, 24/7. If any questions, needs or concerns arise just call us and we will be there at your door to make it right.
Keyless Lock: This home is equipped with a Smart Lock, allowing easy, secure access to your property at check-in and throughout your stay. There's no need to check in at a separate location!
What's Included: Every home is stocked with all your household essentials, high quality sheets and towels, and a starter kit of Aveda bathroom products, and an ample supply of laundry detergent, trash bags, dish soap, tissues, etc.
We're Following the Rules: This vacation rental is professionally managed and follows all local & state tax rules. Your reservation total includes all applicable taxes, cleaning fee, and Accidental Property Damage Protection.
Guest will be required to sign a Winter Park Lodging Company rental agreement within 48 hours of booking.
The Winter Park Lodging Company Difference
24/7 Local Help: Book with confidence knowing that the rates, images and details published on this property are 100% accurate. We are conveniently headquartered in Winter Park, this provides us with a local advantage to take care of any issue or need that may arise during your stay, 24/7. If any questions, needs or concerns arise just call us and we will be there at your door to make it right.
Keyless Lock: This home is equipped with a Smart Lock, allowing easy, secure access to your property at check-in and throughout your stay. There's no need to check in at a separate location!
What's Included: Every home is stocked with all your household essentials, high quality sheets and towels, and a starter kit of Aveda bathroom products, and an ample supply of laundry detergent, trash bags, dish soap, tissues, etc.
We're Following the Rules: This vacation rental is professionally managed and follows all local & state tax rules. Your reservation total includes all applicable taxes, cleaning fee, and Accidental Property Damage Protection.
Guest will be required to sign a Winter Park Lodging Company rental agreement within 48 hours of booking.
Languages:
English
Premier Host
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